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Posted by Parveen Dhupar on August 15, 2018


Read Part 3 here! 

Over the last three editions of this series, I have shared tactical reasons why entrepreneurs might lose sleep at night. These topics range from millennials in the workplace, hiring great talent, and in my last article, managing cash flow. While these topics are incredibly important and are the source of sleepless nights for many entrepreneurs, they also all have solutions. Today, I want to tackle a topic that is less tactical, more personal, and a topic that no guru or expert can battle for you – fear and failure. After all, being an entrepreneur often means taking big risks, and that can be scary! 

In November of last year, I took a family trip to Arizona. I didn’t know it at the time, but I was in for a challenge that would physically translate the mental struggle entrepreneurs face with fear and failure when we decided to hike Camelback Mountain. It was on this hike that I realized how the physical struggle I was experiencing in that moment, was a lot like the mental one I have been battling for years:


We all have a little bit more to give. Just when I thought I couldn’t possibly go on, I did. Our goal was to make it halfway up the mountain. When we got there, I knew we could go further. This is true for many entrepreneurs. We spend a lot of time focusing on the next project, the next pitch or the new client, raising the bar on sales targets and suddenly when we get there we want more, and our drive keeps pushing us towards bigger goals.


Make decisions swiftly and confidently. We had different options of trails to take throughout our climb. What appeared easy at first got harder ahead. There was no one right path, but we were confident that each one led to the top, and the same is true for business. While doing the research and weighing your options is important, at the end of the day trusting your own foundation of knowledge needs to be second nature. As entrepreneurs, we make decisions every day and agonizing over every single one can be a debilitating habit. 


While no one plans to fail, it is just that they fail to plan. I will admit, I was not prepared for this hike. I didn’t have enough water, gloves or hiking shoes. Looking back, of course there are things I had wished I did or could have done differently, and I have the same thoughts as I look back on my last 20 years as a small business owner. The important thing here is to take what you can from those experiences and move on. We can’t change the past, but we can learn from it, and teach from it too… 


Thoughts become things. As soon as you let fear into your mind, you begin to fail. We never thought of fear throughout our climb. As a small business owner, wandering down the negative side of “what if” used to be an all-consuming event for me. What if the deal doesn’t go through? What if the market does this or that? These thoughts don’t serve me right now, and while understanding risk is important, your world should not be controlled by hypotheticals. I combat these thoughts by staying focused on the big picture, referring to my strategic plan and consciously releasing fear whenever it creeps back in. 

Entrepreneurs work around the clock. Even on vacation, you may be like me and find yourself drawing parallels to how climbing a mountain is a lot like running a business. Sure, it isn’t easy, but the reward can be truly spectacular. 

What keeps you up at night? Let's talk!